Substituent effects on the pK a values and rates of hydrolysis of arylmethylene-erythromycylamines

Autor:	David M. Rackham, Anthony F. Cockerill, Eric Wildsmith, M. F. Ellis
Rok vydání:	1973
Předmět:	Steric effects chemistry.chemical_compound Hydrolysis Hammett equation Chemistry Stereochemistry Substituent Ring (chemistry) Medicinal chemistry
Zdroj:	Journal of the Chemical Society, Perkin Transactions 2. :173
ISSN:	1364-5471 0300-9580
DOI:	10.1039/p29730000173
Popis:	The pKa values and rates of hydrolysis of a series of N-benzylidene derivatives of the macrolide antibiotic, erythromycylamine (I) have been measured. Anomalies in the correlations of the pKa values with the Hammett equation and of the mechanism of hydrolysis with that of an analogous series of N-benzylidene-1,1-dimethylethylamines have been explained in terms of steric and electronic interactions involving the macrolide ring and the unusual effect of ortho-methoxy-substituents.
Databáze:	OpenAIRE
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